← How to Get a Girlfriend with Connell Barrett
How to Get a Girlfriend with Connell Barrett
7 Make-or-Break Dating Moments to Either Win Her Interest… Or Lose It
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There are pivotal moments in dating that determine whether you create romantic sparks with a woman or lose your chance with her entirely. In this episode of “How to Get a Girlfriend,” dating coach and bestselling author Connell Barrett breaks down 7...
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To approach or not to approach. That is the question Shakespeare should have written about dating. Welcome back to the how to Get a Girlfriend podcast. I'm your host, dating coach Connell Barrett. Helping you attract incredible women and getting a great partner, a great girlfriend, and doing it with authenticity. No sketchy, weird pickup artist moves needed. I'm so excited today. I have a really fun episode. If you hear jingling in the background, by the way, I am a new cat dad. I have these two little orange tabbies who are literally running around my apartment, my studio slash apartment, playing with cat toys. So if you hear a little bell going off, you're hearing my two little orange boys. Today's episode, I want to talk about make or break moments, moments of truth, make or break moments that determine whether or not you and that woman end up as a couple or at least end up having some kind of romantic connection. A win win where you're both into each other, you date for a while, you hook up, you fall in love. There are make or break moments that happen early in the dating and courtship process that determine your success. They're subtle. Often they're very subtle. Sometimes they're literally invisible. And I just want you to be aware of them. Here are seven of the most common make or break moments. I'm going to run you through each one. We've got approaching. We've got online dating. We've got flirting and how to handle yourself on a date. Let me start with a story, though. I want to talk about the first make or break moment, which is the moment you decide you either will or won't approach that woman. I remember many years ago, I'm in a Starbucks on Park Avenue, 29th street in New York City on a Sunday afternoon. I had never approached a woman before, but that day I saw this really pretty brunette sitting by herself. She's on her phone. I remember she looked like Katie Holmes, who was my crush at the time. She was my late 2000s crush. And I walked over to her seat, her table, and I wanted to approach her, but I didn't. I literally just walked around her table a couple times trying to think of the right thing to say, not coming up with anything good enough. And I went and sat down thinking, okay, let me try again. I was worried about other people seeing me and wondering if how bad it might feel if I bothered her and creeped her out. And I was also just worried that I would say the wrong thing and she wouldn't want to talk to me and that would make me feel shitty. So I sit Back down. I'm trying to think of something better to say. And five or 10 minutes later, she walks up, leaves. And I remember thinking, gosh, if I could have only gone and approached her, I might be on a date with her tomorrow. I might have her in my life. But I don't. Now she's going off to meet some other guy, probably, and it won't be me. So these are high stakes moments. These are make or break moments that determine whether or not you find love. That's why I'm going into these. They're important. So make or break moment number one is deciding to approach or not to approach. To approach or not to approach. That is the question Shakespeare should have written about dating. And there are probably hundreds of times a year, dozens of times a month, when you see a woman you would love to talk to, but you don't do it. And that's the make or break moment. So here's a quick story of me, of me doing the right thing because I shared that failure of mine at Starbucks. I want to share a success. Fast forward a few years. I've got a lot of approaches under my belt. I'm not yet a dating coach, but I'm getting pretty good at this. And I saw a woman out in a park here in New York City, and I. I actually had just wanted to, but failed to approach a different woman. And I was so mad at myself, I said, ugh, Connell, damn it. You are going to approach the next most attractive, the next cute girl you see. And I see walking across the street in the shadow of the Flatiron Building here in New York City. I see this cute, curvy woman. She was wearing a pencil skirt, she had a fedora on. And I remember I was listening to Frank Sinatra song on my phone, and I saw this woman and I thought, oh, my gosh, this was meant to be. She's got a fedora on. I'm listening to Frank. This was meant to be. So I was nervous, but I made a decision. I said, let's go, let's go talk to her. I walked up to her and I even had something ready to say. I was going to say something about, hey, I like your fedora. I'm actually listening to a Frank Sinatra song that might have worked. Well, I get up to her and a cat calling dude on the street shouts out at her mo. Like I'm literally three feet away from her. A cat calling dude says, yells toward her, hey, baby, I like the way you walk. And I heard that I made eye contact with her. She understood what was happening here. And I walked over and said, hey, I just want to apologize for my dad. He does not know how to talk to women. Just in the moment, right? And she threw her head back, laughed. She was. And she said, you're way better at hitting on girls than he is. And she was smiling ear to ear. We stood and Talked for about 10 minutes and we were on a date. Two nights later. Two nights later we went to an improv show on a first date and had a great time and we ended up becoming boyfriend girlfriend. Her name is Catherine. Hi, Catherine, if you're listening. And what an amazing moment that was for me. That was powerful for me because I realized the big truth I realized was that you might think that you, quote, can't approach a woman because it's uncomfortable. You can you simply decide to you make an adult decision using good old fashioned courage. I was actually pretty nervous as I walked up to her, but I did it anyway. And I could have approached that girl at Starbucks a few years earlier, but I chose not to. And that's the takeaway I want to give you with this first make or break moment is you can decide to approach any woman you want to at any time. You can't decide it's going to feel good. You can't decide, you won't be nervous. You can't certainly can't know for sure that it will turn into a phone number or a date. But that's a make or break moment and you're in control of it. Okay. You can decide to talk to any woman you want to. And had I not walked up to Kat that day, I would have lost out on this really great, sweet, warm, beautiful young woman who became my girlfriend for about six months. So that was a make or break moment. So yeah, takeaway for you is look for those make or break approaching moments and decide to do it even if you're uncomfortable. Okay. Make or break moment number two is also about approaching. Here's a quick story. Fast forward a few more years. I'm now a professional dating coach. It's in the mid teens and I'm in a park in New York City with a couple of clients. One of the things I do with my clients is we go out and approach girls together. And I'm out with two clients, Joel and Chris, I believe was the second fellow's name. But I remembered the Joel story. So I'm giving Joel and Chris approaching instructions. Go talk to her. Go say this. And Joel walks over to a really pretty woman. They're sitting on the bench. The conversation's going really well. She's smiling, she's laughing. It couldn't be going better. I realized that Joel doesn't seem to need me. So I leave the scene for a couple minutes. I go find Chris. I come back about 10 minutes later, and that young lady is sitting by herself, really pretty, brunette, sunglasses on, just sitting in a park, reading a book, I think. And I'm like, okay, that ended. Let's. I wonder what happened. I look around for Joel, and I see this bench about 50 yards away, around. Around this little curve in the park. This is Madison Square park, by the way. And I look around, and I see Joel sitting by himself, and his face is in his hands. He's clearly having some kind of little mini crisis. And I'm thinking, oh, my God, what happened? What did she say? What did she do? Did she call the cops? Did she tell him to get away? Did she call them names? I walk over to Joel and I say, dude, what happened? He said, I screwed up. I'm such an idiot. I said, what happened? He said, well, conversation was going great, and I wanted to ask her out, but I just didn't. I just said, well, nice meeting you. And then I walked away. And I'm so stupid. I'm such a chicken. And I gave him a little pat on the back. Literally, I think. And. And I said, okay, we'll talk about this later, but before we'll break this down later, she's sitting right over there. And I said to him, I asked him a simple question that I think is a really powerful question. I said, if you knew you could not fail, and by walking back over there, what would. What would you say if you knew you couldn't fail? He stood up. He got a little bit of hope in his eyes and a little bit of determination. He said, you know what? If I couldn't fail, I'd walk over there and I'd say to her, I forget her name. Let's say it was Alice. I'd say to her, alice, I wanted to ask you out a few minutes ago, but I wimped out because you're so pretty, But I had to come back and ask you if you want to go on a date. And I said, boom, there you go. Go over and say those exact words, because those words are true. They're genuine, they're authentic. So he walks over with a head of steam, and I'm about 50 yards behind him. I couldn't hear because too far away, but I could see it. So it played out like a. Like a silent movie because I couldn't hear. I couldn't hear the audio. He walks over, he stands up. He stands above her. She looks back up, smiles. Because, oh, yeah, Joel, the guy I was just talking to. And I hear him say the thing. I'm sorry. I see him say the thing. I couldn't hear it. And I watch her face break out into a big, big, big grin. And she puts her hand out as if to say, give me your phone. And she takes his phone and puts her numbers, puts her number in the phone, and they set up a date. So the make or break moment I'm talking about here is once you start approaching women, once you finally start to do it, there's going to be a second moment of truth, a second make or break moment, which is just making that choice to play to win and not settle for a good conversation. Make sure you ask for the date. Joel was settling for a good conversation. And that lower self, that voice of self doubt, will say to you, oh, my gosh, I'm approaching a girl and it's actually going pretty good. I don't want to ruin this good feeling. So I am going to just settle for a nice conversation. But if you do that, you're going to lose the chance of even meeting that woman. Why are we doing this? In large parts, you can find love, get dates. So learn from Joel. It's going to feel so much better if you just go for the phone number. Go for the date. By the way, there are times when you're not. When you're going to go for a number, go for a date, and she won't be interested or she'll have a boyfriend. That's fine, too. You might be surprised how good you feel when you just speak the truth. Cool. All right, let's go to make or break moment number three. This. Let's switch to the. To the dating apps. I call this the online dating profile deal breaker. Here's the make or break moment. The make or break moment is she's on. She's on your profile. And you probably think that it's all about the photos. If you have good photos, you'll succeed. If your photos aren't good, you'll fail. And that's not quite true. Really good, attractive photos that show your interesting, normal, authentic life that will get a woman swiping through the rest of your profile. But the make or break moment is when she then looks at your bio and your prompts and she says, oh, yeah, this guy's my type. Or this guy made me laugh. There's some personality, there's some humor, there's some realness that says to her, this is my kind of guy. Or at least, at the very least, says to her, says to her, a date with him would be fun. So that's the make or break moment. It's what a woman experiences while looking at your profile. I've had a lot of women say to me and my clients on dates, they've said things like, you know why I'm on a date with you? You made me laugh on your profile. That just got me giggling. That thing you wrote about X or Y, the joke. Or they said things like, oh, I like your photos, but what really made me want to meet you was I just wanted a date with a guy who likes some of the things I like, musical theater. I'm a theater nerd, by the way, so I've had a few dates with women over the years who are into theater, into the arts. So your make or break moment, the make or break moment is the moment you give women on your profile. So you're going to want to make sure. Of course, you want to have good photos. That's absolutely essential. At the same time, you're also going to want at least one prompt that makes a woman laugh, literally makes her laugh out loud. And also one part of your bio that conveys a clear, specific glimpse into who you are as a man so she can understand, what kind of guy is this? And in terms of a funny prompt, the one that has worked really well for me lately is, this is on my hinge and my bumble right now. It says, if you like tall, handsome, charming, funny, financially secure, humble, successful men who love dogs and kids, then you should be my brother. A lot of women laugh at that, and they. I get a lot of messages saying, hey, I really want to meet your brother, Connell. Is he free? And I might say, ah, sorry, my brother is happily married, but I'm available. And there's something about making a woman laugh that gets the matches and that gets her to swipe right on you and really consider a date with you. So remember, good photos will get her looking at your profile, by the way, bad photos will get women swiping left in less than 2 seconds. Good photos will get her swiping through your profile. What will seal the deal is one piece of your bio that makes her laugh because your authentic sense of humor is coming out. And also that she gets a sense for who you are as a guy. Okay, make or break moment number four. Let's go to the first date. Turning things from friendly to flirty or making sure the date is. Is more than just friendly, it's flirtatious. In other words, making it what I call man to woman communication. You know that you have to flirt, right? But you might not be doing it. You might be playing it safe. And I want to share a story about my client Trevor. Trevor. This is in my book. It's a pretty good story. So Trevor came to me because he was in the friend zone. And Trevor had like literally six, seven, eight dates in a row where he heard almost verbatim, hey, you seem like a great guy. I'm just not feeling it from. From women after first dates, like nine out of 10 times he was hearing that or something like that. And so he and I started working together and I gave him sort of the. The way to. The way to flirt on a first date. And the vibe. The channel I call the. The flirting sort of context or frame. I call it man to woman communication. And you might think that flirting is just about giving a woman one compliment or that if you just make good conversation, good friendly conversation on a date, that hopefully will be enough because she likes you for you. It might not. It really might not. And it wasn't for Trevor. Trevor was being funny. He actually is funny, but he wasn't being what I call man to woman. Let me pull back for a second and share this. There are only three social channels to communicate on which to communicate with women. Here are the three channels. Every single conversation you have with a woman falls into one of three channels. One channel is friend to friend, the way you talk to friends. The second channel is business transactional. You know, the way you communicate at work or in a transactional business setting. Like the waitress is coming over, she's talking about the food order. She's not talking personally with you, probably. And the third channel is mantowoman communication. So if you are ever struggling with not getting second dates, if you're in the quote unquote friend zone, it's very likely because you are talking in a more friendly way and. Or transactional, logical way, not in a man to woman way. And that's what Trevor was doing wrong. So I gave Trevor some marching orders. He has a first date with a woman named Becca. Becca is a chef here in New York City and she had had several dates with guys that didn't go well. She basically was putting guys in their friend zone left and right. She didn't want to. She just wasn't feeling what women need to feel as I watch my orange tabby do backflips. Anyway, so Becca and Trevor go on the first date and there's some really important couple make or break moments. There was a make or break moment early on. One of the tips I gave him for being man to woman is, as men, it's our jobs to lead a date to a good place. It's like leading a dance. And early on in the date, there was a point where she was telling a fairly long story that just wasn't really helping the date. Like a two or three or four minute story about, I don't know, shopping. Kind of a girly, a girl woman topic. There's nothing wrong with those topics. But he listened for two or three or four minutes and realized, oh my gosh, I'm not being honest with her. This story is boring. So he, he felt nervous about this, but he, he basically, he jumped in and interrupted her and said, with a smile on his face, he said, hey, I got to be honest with you. I've. I've totally lost interest in that story. I almost fell asleep. But listen to what happened to me today. And he tells a story about something that happened to him that day. He told me that she gave him this look. She cocked her head and gave him a look as if to say, did you just shush me? And take over the conversation? But the thing is, the crazy thing is if she was doing it more, the look was a sense of respect, not, how dare you interrupt me now, by the way, the lesson here is not to interrupt women and cut them off. That is not the lesson. No bueno. That's not what I teach. However, the reason that worked with Becca, and it did work, was that she basically said, okay, finally, a guy who's not afraid to tell the truth to me, who's not afraid to take a risk, a social risk for the betterment of the date. He also did other good things on the date. He was a little bit teasing, a little bit snarky, and also very sincere and genuine. And he let her know when the time was right that he thought she was really sexy and cute. So he was turning up this. These man to woman dials. By the end of their date, Becca was sitting on Trevor's lap. They were kissing, making out. This is at a bar. Excuse me? This is at a, as I understand it, like a kind of a small corner, candlelit bar. Corner bar in a neighborhood in New York City. This is, this is not like a Club at 1am on a Saturday. It's like Date night on a Thursday night. They're making out, she's sitting on his lap, and then she asks him out for the second date. And their second date was a couple's massage. Just so happened she had a coupon or some kind of credit for a couple's massage. And she said, you know what we should do for a second date? She's sitting on his lap and he said, sure, sounds good. Their second date was a romantic couple's massage. I couldn't make this shit up. So the main takeaway I want you to have from this is your job on a date is to show up authentically, to be present, to be yourself. It's also to lead and to get on that man to woman wavelength. If you get on that man to woman wavelength, then you're not going to get in the friend zone very often, maybe never. And you're going to have some really great dates with women. I can't promise you you're going to have a romantic R or X rated couples massage for a second date. But. But actually, if you work with me, you might. Okay, let's go to make or break moment number five. Let's talk about make or break moment number five. Do or die moment. Keeping the text momentum going between dates. This can cost you a date. Sadly. I have a good buddy, my. My client friend, Nick. Nick recently matched with a woman on Bumblebee. Classic match situation. Bread and butter. He's doing everything perfectly. Got the date set up, got off of the app, off of Bumble, set up the date for about six days away. That was the day they were both free. Let's say that's on a Sunday and their dates on Friday night. Okay? He goes quiet, no texting. He does not text her the rest of Sunday, Monday, Tuesday, Wednesday, Wednesday or Thursday. Their date is Friday night. He doesn't text her at all. And come Friday morning or late morning, he shoots her a text and say, just says, hey, just checking to make sure we're still on for tonight. And she writes him back. Honestly, she said, to be honest, I've lost interest. I didn't hear from you and you don't seem like you're that into this, so I made other plans for tonight. Sorry. And she was well within her rights to say that I'm on her side here. And it was a really valuable lesson for Nick to keep the text cadence going. It's a make or break moment. Once you and she agree to the date, you don't know for sure. She won't flake and flaking Is usually not the woman's fault. It's usually a result of the mistake the man makes by going quiet. Either texting poorly or not texting at all. So you want to keep a cadence going during dates. It's not enough to just set up a date. Most women like at least a little bit of messaging leading up to a date on bare minimum, just to keep a social connection going. Bare minimum, which he wasn't doing. As an added bonus, what I love doing with my clients is helping them not just keep the texting momentum going between date, between setting up the date and date number one, but to dial up attraction. I love sending a message the day before a date. You know, hey, Rebecca, I got a brand new haircut, so I'm gonna look extra handsome tomorrow night. You better bring your A game. You know, something little fun, flirty, playful messages like that can. Can get women excited. Not only not cancel on you, but actually get excited about the date. I like to look at the text leading up to a date as movie trailers designed to get her excited, get both of you excited. And the date is the. The main feature. So that's a make or break moment. Very subtle. Don't go quiet. And the same. It's not just about between setting up the date and date number one. Same goes for date number one. Between date number one and date number two, same thing can happen. So keep it. Keep a texting cadence going. At least one message every day or two. All right, let's go to make or break moment number six, which is how to handle a woman's tests. Different women. Most women on some level, are trying to gauge your. For lack of a better term, your integrity. Not integrity as a man, but your strength, your solidity, your value, your strength as a man. And so there's a term in the world of dating gurus. You may or may not know this term. It's called shit test. A lot of women give guys, quote, shit tests. That's not a bad thing. It's actually something women have to do. That's the other term I learned back in the day was congruence tests, Meaning she wants to find out if you are congruent and as. As confident and cool in reality as you are projecting that those two things are aligned and congruent. Let's call them shit tests. A shit test is just a woman's way of finding out, okay, is this guy. Is this guy man enough for me? Is he man enough for me? And so you want to be aware that shit tests might happen with someone from Some women. And don't think of it as a bad thing, think of it as an opportunity because you passed the test, then she's going to become more into you. Here's an example of a shit test. It can be small. A shit test. My future, my Ben first date, future girlfriend Lorraine. We had a first date and we were talking about Will Ferrell movies and we were talking about snl and she said, so what do you think about Will Ferrell? Do you think he's really overrated? She. It's like she was trying to lead me down that path to see if I would say that. And I said, no, I think he's amazing. He's comedy genius. I love Will Ferrell. Old school, hilarious. And she said, yeah, I love him too. She was trying to see if I was going to say what I thought she wanted to hear. That would have been a mistake. That's a little make or break moment where you can lose a woman by saying the thing, by doing a. By contorting yourself into the position of what you think she wants to hear and see as opposed to just being genuine. Part of why my religion, my philosophy is authenticity, is if you know who you are, what you stand for, what you believe, you don't have to worry about that. You just lead with the truth. And by the way, maybe I didn't like Will Ferrell, that'd be fine, too. I would have told that truth. But Will Ferrell's great. My mistake would have been had I said, oh, no, I love Will Ferrell. He's fantastic when I didn't believe it, or vice versa. So understand that women are looking for chinks in the confidence armor, and they have to do this because she wants to end up with the most incredibly strong, confident guy. So of course she's going to test you. Not every woman. Don't get in your head about this. Don't be defensive. Don't think of it as women are trying to test us. We're all trying to find a really great partner. We all are. And we all have our own screening system for what we want. That's all it is. It's just part of the screening system of many women. By the way, many women do not think about testing guys at all. So case by case basis, but be ready for it. Because when it does happen, if you fail the quote unquote test, then you could lose that girl. And if you pass it, she's going to be more into you because she's going to realize, yeah, this guy is who he says he Is. Okay, let's do one more. Um, this is a good one. I like this one. Here's make or break moment number seven. Whether or not you follow up to an unanswered text message. So you send that text, right? Do you go quiet or do you follow up in a charming way? That's a huge make or break moment. It's so subtle, but it can make the difference between her going on a date with you, intimacy happening, love, possibly happening. It can make all the difference. So that's the moment. The moment to be aware of. You send that text message, you wait one, maybe two days, no response. The mistake would be if you just gave up and made an assumption that she's just not into you. Here's a huge misconception I want to clear up for you. You might think that an unanswered text message means she's not into you. It does not. It just means she didn't see it or she saw it and didn't have time to respond. Or worst case scenario, she saw it and she wants to see if you are persistent. Basically, it's a. It's a more passive test, make or break. Right? Test number six. Make or break number six. Testing her. Testing you. So, yeah, the core truth is, here's where you probably are right now. You send the text message, you might get a little butt hurt. If she doesn't reply, you make a false assumption. Oh, I guess she's not into me. I guess she doesn't like me. No, she's probably just distracted. If she's an attractive, stylish woman with a cool life that's together, she has got a crazy amount of online dating options coming in. If you're on the apps, and even if you're off the apps, if you're just texting each other, she still has options, and there's a lot of stimuli hitting her and you just want to follow up. So here's the solution to this. The solution is what I call the three times rule. The three times rule, which is I would never give up on a woman I'm attracted to, interested in. Until three good text messages go unanswered. Three good ones not. Hey, did you get my last message? Hey, are you blowing me off? Hey, am I gonna stay a virgin, ginger forever? No. 3 Good humor, heart jokes. I can't tell you how simple this little make or break moment is and how it can change everything. So send a second message and a third message and just make sure each one is what I call a value text, meaning you're bringing value to her. You're trying to make her smile. You're doing your best to stay on her mind. There was a woman I was trying to meet up for a date once on Bumble. And she's beautiful. She's model attractive in my opinion. She's an artist. She is a dynamite 9.9999. 9 out of 10. And she went quiet a couple times. One or two messages didn't get a response. But I didn't give up. I said, you know what? Send that third message. Connell, send that third message because she's an artist. So here's an example of a value text. She didn't answer a couple messages. And then I remember thinking, all right, what does. What does Jennifer like? What does she care about? She's into modern art. Art installation stuff. I knew that. So I remember I took a photo of a piece of outdoor art in New York City. Like a cow that covered in newspaper or something like that. A funky little art installation. Took a photo of it, and I sent it to her. And I said, okay, pop quiz, artist. Is this A, a brilliant work of art or B, just a fucking cow? Inquiring. Inquiring minds want to know. And she wrote back right away. Lol. Oh, my God, I love that. That is such a cool piece of art. And then she said, sorry I didn't get back to you. I've been really busy with blah, blah, blah. And the conversation was back on. And that led to us dating. I would not have had a date with her and dated her. This led to a relationship. And that wouldn't have happened had I not sent the third message. So use the three times rule. Do not assume any woman is has lost interest just because it's one. One unanswered text message. Here's what women respond to by text. Think of it this way. Here's your secret formula. Persistence plus charm equals dates. Persistence plus charm equals dates. So, yeah, three times roll. I've had multiple women say to me things like, one woman. This is almost a verbatim quote. I sent that third message after the first two. She didn't answer. I sent her something snarky and funny. I wrote something like, dear Diary, Megan has gone quiet again. Do you think she found out I still live with my mom and dad thinking emoji, something like that. I'm just having fun, letting my sense of humor shine or trying to. And she wrote back, lol or lo fi. Lo fing L. Oh, my God, that was so funny. By the way, I really admire how persistent you are. I like it. Here's my number. She literally said, I wanted to see how persistent you are. A couple women have said that to me over the years, which means many more are thinking it's so don't give up. After one unanswered text, send a second, send a third. Make them fun, funny, authentic, seeking to give value to her. Okay, and this I rarely say always or never. I don't make guarantees to a. To a large audience. But I can almost guarantee that if you follow the three times rule, you will have dates. And you will have romantic connections that you will lose out on if you don't follow the three times rule. Because persistence plus charm equals dates. All right, thank you so much for listening. Until next time. Oh, by the way, if you would like to talk to me or somebody from my team about how my coaching works, because you want to make sure that you meet these make or break moments and that you make the approach. You flirt on the date, you play to win, not playing to lose, go to datingtransformation.com I do coaching men and women, primarily men. But I'm coaching women now as well. And if you are interested in learning how my coaching works, you can do a free call datingtransformation.com and you and I might just talk soon. All right, Till next time, Sam.